Compound and organic light emitting diode comprising same

ABSTRACT

Provided is a compound of Chemical Formula 1: 
     
       
         
         
             
             
         
       
         
         
           
             wherein:
           Y is O or S; X1 to X3 are each N or CH, and one or more of X1 to X3 is N; and   Ar1 to Ar4 are the same as or different from each other, and each independently is an aryl group having 6 to 20 carbon atoms that is unsubstituted or substituted with nitrile or a heteroaryl group having 2 to 20 carbon atoms; or a tricyclic heteroaryl group having 2 to 20 carbon atoms that is unsubstituted or substituted with an aryl group having 6 to 20 carbon atoms,
 
and an organic light emitting device including the same.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a National Stage Application of InternationalApplication No. PCT/KR2019/003663 filed on Mar. 28, 2019, which claimspriority to and the benefits of Korean Patent Application No.10-2018-0035676, filed with the Korean Intellectual Property Office onMar. 28, 2018, the entire contents of which are incorporated herein byreference.

TECHNICAL FIELD

The present specification relates to a compound, and an organic lightemitting device including the same.

BACKGROUND

An organic light emission phenomenon generally refers to a phenomenonconverting electrical energy to light energy using an organic material.An organic light emitting device using an organic light emissionphenomenon normally has a structure including an anode, a cathode, andan organic material layer therebetween. Herein, the organic materiallayer is often formed in a multilayer structure formed with differentmaterials in order to increase efficiency and stability of the organiclight emitting device, and for example, can be formed with a holeinjection layer, a hole transfer layer, a light emitting layer, anelectron transfer layer, an electron injection layer and the like. Whena voltage is applied between the two electrodes in such an organic lightemitting device structure, holes and electrons are injected to theorganic material layer from the anode and the cathode, respectively, andwhen the injected holes and electrons meet, excitons are formed, andlight emits when these excitons fall back to the ground state.

Development of new materials for such an organic light emitting devicehas been continuously required.

BRIEF DESCRIPTION Technical Problem

The present specification is directed to providing a compound, and anorganic light emitting device including the same.

Technical Solution

One embodiment of the present specification provides a compound ofChemical Formula 1:

In Chemical Formula 1:

Y is O or S;

X1 to X3 are each N or CH, and one or more of X1 to X3 are N;

Ar1 to Ar4 are the same as or different from each other, and eachindependently is an aryl group having 6 to 20 carbon atoms unsubstitutedor substituted with nitrile or a heteroaryl group having 2 to 20 carbonatoms; or a tricyclic heteroaryl group having 2 to 20 carbon atomsunsubstituted or substituted with an aryl group having 6 to 20 carbonatoms.

Another embodiment of the present specification provides an organiclight emitting device including a first electrode; a second electrodeprovided opposite to the first electrode; and one or more organicmaterial layers provided between the first electrode and the secondelectrode, wherein one or more layers of the organic material layersinclude the compound of Chemical Formula 1.

Advantageous Effects

A compound according to one embodiment of the present specification canbe used as a material of an organic material layer of an organic lightemitting device, and by using the same, efficiency can be enhanced, alow driving voltage can be obtained, and/or lifetime properties can beenhanced in the organic light emitting device.

DESCRIPTION OF DRAWINGS

FIGS. 1 and 2 illustrates organic light emitting devices according toembodiments of the present specification.

REFERENCE NUMERALS

-   -   1: Substrate    -   2: Anode    -   3: Light Emitting Layer    -   4: Cathode    -   5: Hole Injection Layer    -   6: Hole Transfer Layer    -   7: Electron Blocking Layer    -   8: Electron Transfer Layer    -   9: Electron Injection Layer

DETAILED DESCRIPTION

Hereinafter, the present specification will be described in more detail.

One embodiment of the present specification provides a compound ofChemical Formula 1.

By having an electron deficient group-electron deficient group-electrondonating group structure, the compound of Chemical Formula 1 of thepresent specification is capable of controlling a total electronquantity in a device and thereby maximizing efficiency and lifetime.

In the present specification, a description of a certain part“including” certain constituents means capable of further includingother constituents, and does not exclude other constituents unlessparticularly stated on the contrary.

In the present specification, a description of one member being placed“on” another member includes not only a case of the one member adjoiningthe another member but a case of still another member being presentbetween the two members.

Examples of substituents in the present specification are describedbelow, however, the substituents are not limited thereto.

The term “substitution” means a hydrogen atom bonding to a carbon atomof a compound is changed to another substituent, and the position ofsubstitution is not limited as long as it is a position at which ahydrogen atom is substituted, that is, a position at which a substituentcan substitute, and when two or more substituents substitute, the two ormore substituents can be the same as or different from each other.

In the present specification, the term “substituted or unsubstituted”means being substituted with one, two or more substituents selected fromthe group consisting of hydrogen, deuterium, a nitrile group, asubstituted or unsubstituted alkyl group, a substituted or unsubstitutedcycloalkyl group, a substituted or unsubstituted alkoxy group, asubstituted or unsubstituted aryloxy group, a substituted orunsubstituted aryl group, and a substituted or unsubstitutedheterocyclic group, or being substituted with a substituent linking twoor more substituents among the substituents illustrated above, or havingno substituents. For example, “a substituent linking two or moresubstituents” can include an aryl group substituted with an aryl group,an aryl group substituted with a heteroaryl group, a heterocyclic groupsubstituted with an aryl group, an aryl group substituted with an alkylgroup, and the like.

In the present specification, the alkyl group can be linear or branched,and although not particularly limited thereto, the number of carbonatoms is preferably from 1 to 30. Specific examples thereof includemethyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl,tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl,isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methyl-pentyl,2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl,heptyl, n-heptyl, 1-methylhexyl, cyclopentyl-methyl, cyclohexylmethyl,octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl,2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, 1-ethyl-propyl,1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl,5-methylhexyl and the like, but are not limited thereto.

In the present specification, the cycloalkyl group is not particularlylimited, but preferably has 3 to 30 carbon atoms. Specific examplesthereof include cyclopropyl, cyclobutyl, cyclopentyl,3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl,3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl,3,4,5-trimethylcyclohexyl, 4-tert-butyl-cyclohexyl, cycloheptyl,cyclooctyl and the like, but are not limited thereto.

In the present specification, the alkoxy group can be linear, branchedor cyclic. The number of carbon atoms of the alkoxy group is notparticularly limited, but is preferably from 1 to 30. Specific examplesthereof can include methoxy, ethoxy, n-propoxy, isopropoxy, i-propyloxy,n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy,isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy,n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and thelike, but are not limited thereto.

In the present specification, the aryl group is not particularlylimited, but preferably has 6 to 30 carbon atoms, and the aryl group canbe monocyclic or polycyclic.

When the aryl group is a monocyclic aryl group, the number of carbonatoms is not particularly limited, but is preferably from 6 to 30.Specific examples of the monocyclic aryl group can include a phenylgroup, a biphenyl group, a terphenyl group and the like, but are notlimited thereto.

When the aryl group is a polycyclic aryl group, the number of carbonatoms is not particularly limited, but is preferably from 10 to 30.Specific examples of the polycyclic aryl group can include a naphthylgroup, an anthracenyl group, a phenanthryl group, a triphenyl group, apyrenyl group, a phenalenyl group, a perylenyl group, a chrysenyl group,a fluorenyl group and the like, but are not limited thereto.

In the present specification, the fluorenyl group can be substituted,and adjacent groups can bond to each other to form a ring.

When the fluorenyl group is substituted,

and the like can be included. However, the structure is not limitedthereto.

In the present specification, the aryl group in the aryloxy group, theN-arylalkylamine group and the N-arylheteroarylamine group is the sameas the examples of the aryl group described above. Specific examples ofthe aryloxy group can include a phenoxy group, a p-tolyloxy group, anm-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6-trimethylphenoxygroup, a p-tert-butylphenoxy group, a 3-biphenyloxy group, a4-biphenyloxy group, a 1-naphthyloxy group, a 2-naphthyloxy group, a4-methyl-1-naphthyloxy group, a 5-methyl-2-naphthyloxy group, a1-anthryloxy group, a 2-anthryloxy group, a 9-anthryloxy group, a1-phenanthryloxy group, a 3-phenanthryloxy group, a 9-phenanthryloxygroup and the like.

In the present specification, the heteroaryl group includes one or moreatoms that are not carbon, that is, heteroatoms, and specifically, theheteroatom can include one or more atoms selected from the groupconsisting of O, N, Se, S and the like. The number of carbon atoms isnot particularly limited, but is preferably from 2 to 30, and theheteroaryl group can be monocyclic or polycyclic. Examples of theheterocyclic group can include a thiophene group, a furan group, apyrrole group, an imidazole group, a thiazole group, an oxazole group,an oxadiazole group, a pyridyl group, a bipyridyl group, a pyrimidylgroup, a triazinyl group, a triazole group, an acridyl group, apyridazinyl group, a pyrazinyl group, a quinolinyl group, a quinazolinylgroup, a quinoxalinyl group, a phthalazinyl group, a pyridopyrimidylgroup, a pyridopyrazinyl group, a pyrazine-pyrazinyl group, anisoquinolinyl group, an indolyl group, a carbazole group, a benzoxazolegroup, a benzimidazole group, a benzothiazole group, a benzocarbazolegroup, a dibenzopyrrole group, an indole group, a benzothiophene group,a dibenzothiophene group, a benzofuran group, a benzoquinolyl group, abenzonaphthothiophene group, a benzonaphthofuran group, aphenanthrolinyl group, an isoxazole group, a thiadiazole group, aphenoxazine group, a phenothiazine group, a dibenzofuran group and thelike, but are not limited thereto.

According to one embodiment of the present specification, the compoundof Chemical Formula 1 is a compound of the following Chemical Formula 2or 3:

In Chemical Formulae 2 and 3, the substituents have the same definitionsas in Chemical Formula 1.

According to one embodiment of the present specification, X1 to X3 areN.

According to one embodiment of the present specification, two of X1 toX3 are N, and the remaining one is CH. For example, X1 is CH, and X2 andX3 are N; or X2 is CH, and X1 and X3 are N.

According to one embodiment of the present specification, Ar1 to Ar4 arethe same as or different from each other, and each independently is anaryl group having 6 to 20 carbon atoms that is unsubstituted orsubstituted with nitrile or a heteroaryl group having 2 to 20 carbonatoms; or a tricyclic heteroaryl group having 2 to 20 carbon atoms thatis unsubstituted or substituted with an aryl group having 6 to 20 carbonatoms.

According to one embodiment of the present specification, Ar1 to Ar4 arethe same as or different from each other, and each independently aphenyl group unsubstituted or substituted with a nitrile group or acarbazole group; a biphenylyl group; a carbazole group unsubstituted orsubstituted with a phenyl group; a dibenzofuran group; or adibenzothiophene group.

According to one embodiment of the present specification, Ar1 to Ar4 arethe same as or different from each other, and each independently is aphenyl group that is unsubstituted or substituted with a nitrile groupor a carbazole group, a biphenylyl group, a carbazole group, adibenzofuran group or a dibenzothiophene group.

According to one embodiment of the present specification, Ar1 to Ar4 arethe same as or different from each other, and each independently is aphenyl group that is unsubstituted or substituted with a nitrile groupor a 9-carbazole group, a biphenylyl group, a 9-carbazole group, a1-carbazole group, a 2-carbazole group, a 3-carbazole group, a4-carbazole group, a 4-dibenzofuran group or a 4-dibenzothiophene group.

According to one embodiment of the present specification, at least oneof Ar1 to Ar4 is a tricyclic heteroaryl group having 2 to 20 carbonatoms, or an aryl group having 6 to 20 carbon atoms that is substitutedwith a nitrile group or a heteroaryl group having 2 to 20 carbon atoms,and the rest are an aryl group having 6 to 20 carbon atoms.

According to one embodiment of the present specification, one of Ar1 toAr4 is a tricyclic heteroaryl group having 2 to 20 carbon atoms, or anaryl group having 6 to 20 carbon atoms that is substituted with anitrile group or a heteroaryl group having 2 to 20 carbon atoms, and therest are an aryl group having 6 to 20 carbon atoms.

According to one embodiment of the present specification, at least oneof Ar1 to Ar4 is a carbazole group that is unsubstituted or substitutedwith a phenyl group; a phenyl group substituted with a carbazole groupor a nitrile group; a dibenzofuran group; or a dibenzothiophene group,and the rest are an aryl group having 6 to 20 carbon atoms.

According to one embodiment of the present specification, one of Ar1 toAr4 is a carbazole group that is unsubstituted or substituted with aphenyl group; a phenyl group substituted with a carbazole group or anitrile group; a dibenzofuran group; or a dibenzothiophene group, andthe rest are an aryl group having 6 to 20 carbon atoms.

According to one embodiment of the present specification, at least oneof Ar1 to Ar4 is a carbazole group that is unsubstituted or substitutedwith a phenyl group; a phenyl group substituted with a carbazole groupor a nitrile group; a dibenzofuran group; or a dibenzothiophene group,and the rest are a phenyl group or a biphenylyl group.

According to one embodiment of the present specification, one of Ar1 toAr4 is a carbazole group that is unsubstituted or substituted with aphenyl group; a phenyl group substituted with a carbazole group or anitrile group; a dibenzofuran group; or a dibenzothiophene group, andthe rest are a phenyl group or a biphenylyl group.

According to one embodiment of the present specification, Ar1 to Ar4 arean aryl group.

According to one embodiment of the present specification, Ar1 to Ar4 arean aryl group having 6 to 20 carbon atoms.

According to one embodiment of the present specification, Ar1 to Ar4 area phenyl group or a biphenylyl group.

According to one embodiment of the present specification, Ar1 to Ar4 area phenyl group.

According to one embodiment of the present specification, at least oneof Ar1 to Ar4 is a biphenylyl group, and the rest are a phenyl group.

According to one embodiment of the present specification, one of Ar1 toAr4 is a biphenylyl group, and the rest are a phenyl group.

According to one embodiment of the present specification, the compoundof Chemical Formula 1 is selected from among the following compounds:

One embodiment of the present specification provides an organic lightemitting device including a first electrode; a second electrode providedopposite to the first electrode; and one or more organic material layersprovided between the first electrode and the second electrode, whereinone or more layers of the organic material layers include the compounddescribed above.

According to one embodiment of the present specification, the organicmaterial layer of the organic light emitting device of the presentspecification can be formed in a single layer structure, but can also beformed in a multilayer structure in which two or more organic materiallayers are laminated. For example, the organic light emitting device ofthe present disclosure can have a structure including a hole injectionlayer, a hole transfer layer, an electron blocking layer, a lightemitting layer, a hole blocking layer, an electron transfer layer, anelectron injection layer and the like as the organic material layer.However, the structure of the organic light emitting device is notlimited thereto, and can include a smaller or a larger number of organicmaterial layers.

For example, the organic light emitting device of the presentspecification can have structures as illustrated in FIG. 1 and FIG. 2,however, the structure is not limited thereto.

FIG. 1 illustrates a structure of the organic light emitting device inwhich a first electrode (2), a light emitting layer (3) and a secondelectrode (4) are consecutively laminated on a substrate (1). FIG. 1 isan exemplary structure of the organic light emitting device according toone embodiment of the present specification, and other organic materiallayers can be further included. In such a structure, the compound ofChemical Formula 1 can be included in the light emitting layer.

FIG. 2 illustrates a structure of the organic light emitting device inwhich a first electrode (2), a hole injection layer (5), a hole transferlayer (6), an electron blocking layer (7), a light emitting layer (3),an electron transfer layer (8), an electron injection layer (9) and asecond electrode (4) are consecutively laminated on a substrate (1).FIG. 2 is an exemplary structure of the organic light emitting deviceaccording to an embodiment of the present specification, and otherorganic material layers can be further included. The compound ofChemical Formula 1 can be included in the hole injection layer, the holetransfer layer, the light emitting layer, or the electron injection andtransfer layer. The compound of Chemical Formula 1 can be preferablyincluded in the light emitting layer.

According to one embodiment of the present specification, the organicmaterial layer includes a hole injection layer, a hole transfer layer oran electron blocking layer, and the hole injection layer, the holetransfer layer or the electron blocking layer includes the compound ofChemical Formula 1.

According to one embodiment of the present specification, the organicmaterial layer includes a light emitting layer, and the light emittinglayer includes the compound of Chemical Formula 1.

According to one embodiment of the present specification, the organicmaterial layer includes a light emitting layer, and the light emittinglayer includes the compound of Chemical Formula 1 as a host of the lightemitting layer.

According to one embodiment of the present specification, the organicmaterial layer includes a light emitting layer, and the light emittinglayer can include the compound of Chemical Formula 1, an additional hostmaterial and an additional dopant material.

According to one embodiment of the present specification, the hostmaterial added to the light emitting layer includes a carbazole-basedcompound and the like.

According to one embodiment of the present specification, the dopantmaterial added to the light emitting layer includes a metal complexcompound such as an iridium-based complex compound.

According to one embodiment of the present specification, when the lightemitting layer include a plurality of hosts, the first host and thesecond host have a mass ratio of 50:50.

According to one embodiment of the present specification, the lightemitting layer includes the dopant in a ratio of 1% to 20% with respectto a total mass of the host and the dopant.

According to one embodiment of the present specification, the organicmaterial layer includes a hole blocking layer, an electron transferlayer, an electron injection layer, or an electron injection andtransfer layer, and the hole blocking layer, the electron transferlayer, the electron injection layer, or the electron injection andtransfer layer includes the compound of Chemical Formula 1.

According to one embodiment of the present specification, the organicmaterial layer can further include one or more layers selected from thegroup consisting of a hole injection layer, a hole transfer layer, anelectron blocking layer, a hole blocking layer, an electron transferlayer and an electron injection layer.

The organic light emitting device of the present specification can bemanufactured using materials and methods known in the art, except thatone of more layers of the organic material layers include the compoundof the present specification, that is, the compound of Chemical Formula1.

When the organic light emitting device includes a plurality of organicmaterial layers, the organic material layers can be formed with the samematerial or with different materials.

For example, the organic light emitting device of the presentspecification can be manufactured by consecutively laminating a firstelectrode, an organic material layer and a second electrode on asubstrate. The organic light emitting device can be manufactured byforming the first electrode on the substrate by depositing a metal, ametal oxide having conductivity, or an alloy thereof using a physicalvapor deposition (PVD) method such as a sputtering method or an e-beamevaporation method, forming the organic material layer including a holeinjection layer, a hole transfer layer, a light emitting layer and anelectron transfer layer thereon, and then depositing a material usableas the second electrode thereon. In addition to this method, the organiclight emitting device can be manufactured by consecutively depositing asecond electrode material, an organic material layer and a firstelectrode material on a substrate. In addition, the compound of ChemicalFormula 1 can be formed into the organic material layer using a solutioncoating method as well as a vacuum deposition method when manufacturingthe organic light emitting device. Herein, the solution coating methodmeans spin coating, dip coating, doctor blading, ink jet printing,screen printing, a spray method, roll coating and the like, but is notlimited thereto.

According to one embodiment of the present specification, the firstelectrode is an anode, and the second electrode is a cathode.

According to another embodiment of the present specification, the firstelectrode is a cathode, and the second electrode is an anode.

As the anode material, materials having large work function are normallypreferred so that hole injection to an organic material layer is smooth.Specific examples of the anode material usable in the present disclosureinclude metals such as vanadium, chromium, copper, zinc and gold, oralloys thereof; metal oxides such as zinc oxide, indium oxide, indiumtin oxide (ITO) and indium zinc oxide (IZO); combinations of metals andoxides such as ZnO:Al or SnO₂:Sb; conductive polymers such aspoly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene](PEDOT), polypyrrole and polyaniline, but are not limited thereto.

As the cathode material, materials having small work function arenormally preferred so that electron injection to an organic materiallayer is smooth. Specific examples of the cathode material includemetals such as magnesium, calcium, sodium, potassium, titanium, indium,yttrium, lithium, gadolinium, aluminum, silver, tin and lead, or alloysthereof; multilayer structure materials such as LiF/Al, LiO₂/Al orMg/Ag, and the like, but are not limited thereto.

The hole injection layer is a layer that injects holes from anelectrode, and the hole injection material is preferably a compound thathas an ability to transfer holes, therefore, has a hole injection effectin an anode, has an excellent hole injection effect for a light emittinglayer or a light emitting material, prevents excitons generated in thelight emitting layer from moving to an electron injection layer or anelectron injection material, and in addition thereto, has an excellentthin film forming ability. The highest occupied molecular orbital (HOMO)of the hole injection material is preferably in between the workfunction of an anode material and the HOMO of surrounding organicmaterial layers. Specific examples of the hole injection materialinclude metal porphyrins, oligothiophene, arylamine-based organicmaterials, hexanitrile hexaazatriphenylene-based organic materials,quinacridone-based organic materials, perylene-based organic materials,anthraquinone, and polyaniline- and polythiophene-based conductivepolymers, and the like, but are not limited thereto.

The hole transfer layer is a layer that receives holes from a holeinjection layer and transfers the holes to a light emitting layer, andas the hole transfer material, materials capable of receiving holes froman anode or a hole injection layer, moving the holes to a light emittinglayer, and having high mobility for the holes are suited. Specificexamples thereof include arylamine-based organic materials, conductivepolymers, block copolymers having conjugated parts and non-conjugatedparts together, and the like, but are not limited thereto.

The light emitting material of the light emitting layer is a materialcapable of emitting light in a visible region by receiving holes andelectrons from a hole transfer layer and an electron transfer layer,respectively, and binding the holes and the electrons, and is preferablya material having favorable quantum efficiency for fluorescence orphosphorescence. Specific examples thereof include 8-hydroxy-quinolinealuminum complexes (Alq₃); carbazole series compounds; dimerized styrylcompounds; BAlq; 10-hydroxybenzo-quinoline-metal compounds; benzoxazole,benzothiazole and benzimidazole series compounds;poly(p-phenylenevinylene) (PPV) series polymers; spiro compounds;polyfluorene, rubrene, and the like, but are not limited thereto.

The light emitting layer can include a host material and a dopantmaterial. The host material can include fused aromatic ring derivatives,heteroring-containing compounds or the like. Specifically, as the fusedaromatic ring derivative, anthracene derivatives, pyrene derivatives,naphthalene derivatives, pentacene derivatives, phenanthrene compounds,fluoranthene compounds and the like can be included, and as theheteroring-containing compound, carbazole derivatives, dibenzofuranderivatives, ladder-type furan compounds, pyrimidine derivatives and thelike can be included, however, the host material is not limited thereto.

The dopant material can include aromatic amine derivatives, styrylaminecompounds, boron complexes, fluoranthene compounds, metal complexes andthe like. Specifically, the aromatic amine derivative is a fusedaromatic ring derivative having a substituted or unsubstituted arylaminogroup, and arylamino group-including pyrene, anthracene, chrysene,peryflanthene and the like can be included. The styrylamine compound isa compound in which substituted or unsubstituted arylamine issubstituted with at least one arylvinyl group, and one, two or moresubstituents selected from the group consisting of an aryl group, asilyl group, an alkyl group, a cycloalkyl group and an arylamino groupcan be substituted or unsubstituted. Specifically, styrylamine,styryldiamine, styryltriamine, styryltetramine and the like can beincluded, however, the styrylamine compound is not limited thereto. Asthe metal complex, iridium complexes, platinum complexes and the likecan be included, however, the metal complex is not limited thereto.

The electron transfer layer is a layer that receives electrons from anelectron injection layer and transfers the electrons to a light emittinglayer, and as the electron transfer material, materials capable offavorably receiving electrons from a cathode, moving the electrons to alight emitting layer, and having high mobility for the electrons aresuited. Specific examples thereof include Al complexes of8-hydroxyquinoline; complexes including Alq₃; organic radical compounds;hydroxyflavon-metal complexes, and the like, but are not limitedthereto. The electron transfer layer can be used together with anydesired cathode material as used in the art. Particularly, examples ofthe suitable cathode material include common materials that have smallwork function, and in which an aluminum layer or a silver layer follows.Specifically, the cathode material includes cesium, barium, calcium,ytterbium and samarium, and in each case, an aluminum layer or a silverlayer follows.

The electron injection layer is a layer that injects electrons from anelectrode, and as the electron injection material, compounds having anelectron transferring ability, having an electron injection effect froma cathode, having an excellent electron injection effect for a lightemitting layer or light emitting material, and preventing excitonsgenerated in the light emitting layer from moving to a hole injectionlayer, and in addition thereto, having an excellent thin film formingability are preferred. Specific examples thereof include fluorenone,anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole,oxadiazole, triazole, imidazole, perylene tetracarboxylic acid,fluorenylidene methane, anthrone or the like, and derivatives thereof,metal complex compounds, nitrogen-containing 5-membered ringderivatives, and the like, but are not limited thereto.

The metal complex compound includes 8-hydroxyquinolinato lithium,bis(8-hydroxyquinolinato)zinc, bis(8-hydroxy-quinolinato)copper,bis(8-hydroxyquinolinato)manganese, tris-(8-hydroxyquinolinato)aluminum,tris(2-methyl-8-hydroxy-quinolinato)aluminum,tris(8-hydroxyquinolinato)gallium,bis(10-hydroxybenzo[h]quinolinato)beryllium,bis(10-hydroxy-benzo[h]-quinolinato)zinc,bis(2-methyl-8-quinolinato)-chlorogallium,bis(2-methyl-8-quinolinato)(o-cresolato)-gallium,bis(2-methyl-8-quinolinato)(1-naphtholato)aluminum,bis(2-methyl-8-quinolinato)(2-naphtholato)gallium and the like, but isnot limited thereto.

The organic light emitting device according to the present specificationcan be a top-emission type, a bottom-emission type or a dual-emissiontype depending on the materials used.

Hereinafter, the present specification will be described in detail withreference to examples. However, the examples according to the presentspecification can be modified to various other forms, and the scope ofthe present specification is not to be construed as being limited to theexamples described below. Examples of the present specification areprovided in order to more fully describe the present specification tothose having average knowledge in the art.

EXAMPLES

According to one embodiment of the present specification, the compoundof Chemical Formula 1 can be prepared according to the followingreaction formulae, however, the preparation is not limited thereto. Inthe following reaction formulae, types and the number of substituentscan be determined by those skilled in the art properly selecting knownstarting materials. As reaction types and reaction conditions, thoseknown in the art can be used.

Synthesis Example Preparation Example 1

1) Synthesis of Compound 1-1

After dispersing 2,4-dichloro-6-phenylpyrimidine (50.0 g, 223.2 mmol)and (3-chloro-2-(methylthio)phenyl)boronic acid (45.1 g, 223.2 mmol)into tetrahydrofuran (500 ml), a 2 M aqueous potassium carbonatesolution (aq. K₂CO₃) (335 ml) and thentetrakis(triphenylphosphine)palladium(0) [Pd(PPh₃)₄] (7.7 g, 3 mol %)were added thereto, and the result was stirred under reflux for 5 hours.After lowering the temperature to room temperature, the result wasseparated into an organic layer and a water layer, and the organic layerwas distilled. The distilled organic material was extracted withchloroform and water, and after distilling the chloroform, the resultwas purified with column chromatography using ethyl acetate and hexane,and then distilled and dried to prepare Compound 1-1 (34.8 g, yield 45%;MS: [M+H]⁺=347).

2) Synthesis of Compound 1-2

After introducing acetic acid (300 mL) to Compound 1-1 (34.8 g, 101mmol), 35% hydrogen peroxide (11.4 g) was introduced thereto, and theresult was stirred for 5 hours at room temperature. To the reactionmaterial, an aqueous NaOH solution was introduced, and after stirringthe result for 20 minutes, ethyl acetate was introduced thereto, and thewater layer was removed. The result was dried with anhydrous magnesiumsulfate, vacuum concentrated and then dried to prepare Compound 1-2(36.4 g, yield 100%, MS: [M+H]⁺=308).

3) Synthesis of Compound 1-3

Compound 1-2 (36.4 g, 101 mmol) was introduced to sulfuric acid (150mL), and the result was stirred for 24 hours at room temperature. To thereaction material, a cold aqueous NaOH solution was introduced, andafter stirring the result for 30 minutes, chloroform was added theretofor layer separation, and the result was washed 3 times with water. Theresult was dried with anhydrous magnesium sulfate, vacuum concentrated,then recrystallized using a mixed solution of tetrahydrofuran and ethylacetate, and then dried to prepare Compound 1-3 (23.3 g, yield 70%, MS:[M+H]⁺=331).

4) Synthesis of Compound 1-4

After dispersing Compound 1-3 (23.3 g, 70.8 mmol) and[1,1′-biphenyl]-4-ylboronic acid (15.4 g, 77.9 mmol) intotetrahydrofuran (250 ml), a 2 M aqueous potassium carbonate solution(aq. K₂CO₃) (105 ml) and then tetrakis(triphenyl-phosphine)palladium(0)[Pd(PPh₃)₄] (2.5 g, 3 mol %) were added thereto, and the result wasstirred under reflux for 4 hours. The temperature was lowered to roomtemperature, and produced solids were filtered. The filtered solids wererecrystallized with tetrahydrofuran and ethyl acetate, filtered, andthen dried to prepare Compound 1-4 (21.0 g, yield 66%; MS: [M+H]⁺=449).

4) Synthesis of Compound 1-5

Compound 1-4 (21 g, 46.9 mmol), bis(pinacolato)diboron (13.1 g, 55.6mmol), potassium acetate (13.8 g, 140.6 mmol), dibenzylideneacetonepalladium (1.4 g, 0.8 mmol) and tricyclohexylphosphine (1.4 g, 1.6 mmol)were introduced to dioxane (200 ml), and refluxed for 12 hours. Afterthe reaction was finished, the result was cooled to room temperature andthen vacuum distilled to remove the solvent. This was dissolved inchloroform, washed 3 times with water, and the organic layer wasseparated and dried with magnesium sulfate. This was recrystallizedusing ethyl acetate while being vacuum distilled to prepare Compound 1-5(20.3 g, yield 80%; MS: [M+H]⁺=541).

5) Synthesis of Compound 1

After dispersing Compound 1-5 (15.0 g, 27.1 mmol) and2-chloro-4,6-diphenyl-1,3,5-triazine (7.2 g, 27.11 mmol) intotetrahydrofuran (150 ml), a 2 M aqueous potassium carbonate solution(aq. K₂CO₃) (40 ml) and then tetrakis(triphenyl-phosphine)palladium(0)[Pd(PPh₃)₄] (0.9 g, 3 mol %) were added thereto, and the result wasstirred under reflux for 4 hours. The temperature was lowered to roomtemperature, and produced solids were filtered. The filtered solids wererecrystallized with tetrahydrofuran and ethyl acetate, filtered, andthen dried to prepare Compound 1 (7.7 g, yield 43%; MS: [M+H]⁺=646).

Preparation Example 2

1) Synthesis of Compound 2-1

After dispersing 4-([1,1′-phenyl]-4-yl)-2,6-dichloro-pyrimidine (50.0 g,223.2 mmol) and (3-chloro-2-(methylthio)phenyl)boronic acid (67.0 g,223.2 mmol) into tetrahydrofuran (500 ml), a 2 M aqueous potassiumcarbonate solution (aq. K₂CO₃) (335 ml) and thentetrakis(triphenyl-phosphine)palladium(0) [Pd(PPh₃)₄] (7.7 g, 3 mol %)were added thereto, and the result was stirred under reflux for 5 hours.After lowering the temperature to room temperature, the result wasseparated into an organic layer and a water layer, and the organic layerwas distilled. The distilled organic material was extracted withchloroform and water, and after distilling the chloroform, the resultwas purified with column chromatography using ethyl acetate and hexane,and then distilled and dried to prepare Compound 2-1 (50.8 g, yield 54%;MS: [M+H]⁺=423).

2) Synthesis of Compound 2-2

After introducing acetic acid (500 mL) to Compound 2-1 (50.8 g, 120.4mmol), 35% hydrogen peroxide (13.6 g) was introduced thereto, and theresult was stirred for 5 hours at room temperature. To the reactionmaterial, an aqueous NaOH solution was introduced, and after stirringthe result for 20 minutes, ethyl acetate was introduced thereto, and thewater layer was removed. The result was dried with anhydrous magnesiumsulfate, vacuum concentrated and then dried to prepare Compound 2-2(52.7 g, yield 100%, MS: [M+H]⁺=439).

3) Synthesis of Compound 2-3

Compound 2-2 (52.7 g, 120.4 mmol) was introduced to sulfuric acid (200mL), and the result was stirred for 24 hours at room temperature. To thereaction material, a cold aqueous NaOH solution was introduced, andafter stirring the result for 30 minutes, chloroform was added theretofor layer separation, and the result was washed 3 times with water. Theresult was dried with anhydrous magnesium sulfate, vacuum concentrated,then recrystallized using a mixed solution of tetrahydrofuran and ethylacetate, and then dried to prepare Compound 2-3 (38.6 g, yield 79%, MS:[M+H]⁺=407).

4) Synthesis of Compound 2-4

After dispersing Compound 2-3 (38.7 g, 95.3 mmol) and phenylboronic acid(12.8 g, 104.9 mmol) into tetrahydrofuran (300 ml), a 2 M aqueouspotassium carbonate solution (aq. K₂CO₃) (143 ml) and thentetrakis(triphenylphosphine)-palladium(0) [Pd(PPh₃)₄] (3.3 g, 3 mol %)were added thereto, and the result was stirred under reflux for 4 hours.The temperature was lowered to room temperature, and produced solidswere filtered. The filtered solids were recrystallized withtetrahydrofuran and ethyl acetate, filtered, and then dried to prepareCompound 2-4 (34.6 g, yield 81%; MS: [M+H]⁺=449).

5) Synthesis of Compound 2-5

Compound 2-4 (34.6 g, 72.2 mmol), bis(pinacolato)diboron (21.6 g, 84.9mmol), potassium acetate (22.7 g, 231.7 mmol), dibenzylideneacetonepalladium (1.3 g, 2.3 mmol) and tricyclohexylphosphine (1.3 g, 4.6 mmol)were introduced to dioxane (200 ml), and refluxed for 12 hours. Afterthe reaction was finished, the result was cooled to room temperature andthen vacuum distilled to remove the solvent. This was dissolved inchloroform, washed 3 times with water, and the organic layer wasseparated and dried with magnesium sulfate. This was recrystallizedusing ethyl acetate while being vacuum distilled to prepare Compound 2-5(27.5 g, yield 66%; MS: [M+H]⁺=541).

6) Synthesis of Compound 2

After dispersing Compound 2-5 (15.0 g, 27.1 mmol) and2-chloro-4,6-diphenyl-1,3,5-triazine (7.2 g, 27.1 mmol) intotetrahydrofuran (150 ml), a 2 M aqueous potassium carbonate solution(aq. K₂CO₃) (40 ml) and then tetrakis(triphenylphosphine)palladium(0)[Pd(PPh₃)₄] (0.9 g, 3 mol %) were added thereto, and the result wasstirred under reflux for 4 hours. The temperature was lowered to roomtemperature, and produced solids were filtered. The filtered solids wererecrystallized with tetrahydrofuran and ethyl acetate, filtered, andthen dried to prepare Compound 2 (11.8 g, yield 66%; MS: [M+H]⁺=646).

Preparation Example 3

1) Synthesis of Compound 3-1

After dispersing 9-(2,6-dichloropyrimidin-4-yl)-9H-carbazole (50.0 g,223.2 mmol) and (3-chloro-2-(methylthio)phenyl)boronic acid (69.9 g,223.2 mmol) into tetrahydrofuran (500 ml), a 2 M aqueous potassiumcarbonate solution (aq. K₂CO₃) (335 ml) and thentetrakis(triphenyl-phosphine)palladium(0) [Pd(PPh₃)₄] (7.7 g, 3 mol %)were added thereto, and the result was stirred under reflux for 5 hours.After lowering the temperature to room temperature, the result wasseparated into an organic layer and a water layer, and the organic layerwas distilled. The distilled organic material was extracted withchloroform and water, and after distilling the chloroform, the resultwas purified with column chromatography using ethyl acetate and hexane,and then distilled and dried to prepare Compound 3-1 (46.6 g, yield 48%;MS: [M+H]⁺=436).

2) Synthesis of Compound 3-2

After introducing acetic acid (400 mL) to Compound 3-1 (46.6 g, 107.1mmol), 35% hydrogen peroxide (12.1 g) was introduced thereto, and theresult was stirred for 5 hours at room temperature. To the reactionmaterial, an aqueous NaOH solution was introduced, and after stirringthe result for 20 minutes, ethyl acetate was introduced thereto, and thewater layer was removed. The result was dried with anhydrous magnesiumsulfate, vacuum concentrated and then dried to prepare Compound 3-2(48.3 g, yield 100%, MS: [M+H]⁺=452).

3) Synthesis of Compound 3-3

Compound 3-2 (48.3 g, 107.1 mmol) was introduced to sulfuric acid (200mL), and the result was stirred for 24 hours at room temperature. To thereaction material, a cold aqueous NaOH solution was introduced, andafter stirring the result for 30 minutes, chloroform was added theretofor layer separation, and the result was washed 3 times with water. Theresult was dried with anhydrous magnesium sulfate, vacuum concentrated,then recrystallized using a mixed solution of tetrahydrofuran and ethylacetate, and then dried to prepare Compound 3-3 (29.2 g, yield 65%, MS:[M+H]⁺=420).

4) Synthesis of Compound 3-4

After dispersing Compound 3-3 (29.2 g, 69.7 mmol) and phenylboronic acid(9.4 g, 76.7 mmol) into tetrahydrofuran (300 ml), a 2 M aqueouspotassium carbonate solution (aq. K₂CO₃) (105 ml) and thentetrakis(triphenylphosphine)-palladium(0) [Pd(PPh₃)₄] (2.4 g, 3 mol %)were added thereto, and the result was stirred under reflux for 4 hours.The temperature was lowered to room temperature, and produced solidswere filtered. The filtered solids were recrystallized withtetrahydrofuran and ethyl acetate, filtered, and then dried to prepareCompound 3-4 (24.7 g, yield 77%; MS: [M+H]⁺=462).

5) Synthesis of Compound 3-5

Compound 3-4 (24.7 g, 53.6 mmol) bis(pinacolato)diboron (15.0 g, 58.9mmol), potassium acetate (15.8 g, 160.7 mmol), dibenzylideneacetonepalladium (0.9 g, 1.6 mmol) and tricyclohexylphosphine (0.9 g, 3.2 mmol)were introduced to dioxane (300 ml), and refluxed for 12 hours. Afterthe reaction was finished, the result was cooled to room temperature andthen vacuum distilled to remove the solvent. This was dissolved inchloroform, washed 3 times with water, and the organic layer wasseparated and dried with magnesium sulfate. This was recrystallizedusing ethyl acetate while being vacuum distilled to prepare Compound 3-5(16.0 g, yield 54%; MS: [M+H]⁺=554).

6) Synthesis of Compound 3

After dispersing Compound 3-5 (15.0 g, 27.1 mmol) and2-chloro-4,6-diphenyl-1,3,5-triazine (7.2 g, 27.1 mmol) intotetrahydrofuran (150 ml), a 2 M aqueous potassium carbonate solution(aq. K₂CO₃) (40 ml) and then tetrakis(triphenyl-phosphine)palladium(0)[Pd(PPh₃)₄] (1.6 g, 3 mol %) were added thereto, and the result wasstirred under reflux for 4 hours. The temperature was lowered to roomtemperature, and produced solids were filtered. The filtered solids wererecrystallized with tetrahydrofuran and ethyl acetate, filtered, andthen dried to prepare Compound 3 (12.5 g, yield 70%; MS: [M+H]⁺=659).

Preparation Example 4

1) Synthesis of Compound 4-1

After dispersing Compound 1-3 (20.0 g, 60.8 mmol) anddibenzo[b,d]furan-4-ylboronic acid (14.2 g, 66.9 mmol) intotetrahydrofuran (200 ml), a 2 M aqueous potassium carbonate solution(aq. K₂CO₃) (91 ml) and then tetrakis(triphenylphosphine)palladium(0)[Pd(PPh₃)₄] (2.1 g, 3 mol %) were added thereto, and the result wasstirred under reflux for 4 hours. The temperature was lowered to roomtemperature, and produced solids were filtered. The filtered solids wererecrystallized with tetrahydrofuran and ethyl acetate, filtered, andthen dried to prepare Compound 4-1 (18.0 g, yield 64%; MS: [M+H]⁺=463).

2) Synthesis of Compound 4-2

Compound 4-1 (18 g, 39.0 mmol) bis(pinacolato)diboron (10.9 g, 42.9mmol), potassium acetate (11.5 g, 116.8 mmol), dibenzylideneacetonepalladium (0.7 g, 1.2 mmol) and tricyclohexylphosphine (0.7 g, 2.4 mmol)were introduced to dioxane (200 ml), and refluxed for 12 hours. Afterthe reaction was finished, the result was cooled to room temperature andthen vacuum distilled to remove the solvent. This was dissolved inchloroform, washed 3 times with water, and the organic layer wasseparated and dried with magnesium sulfate. This was recrystallizedusing ethyl acetate while being vacuum distilled to prepare Compound 4-2(17.5 g, yield 81%; MS: [M+H]⁺=555).

3) Synthesis of Compound 4

After dispersing Compound 4-2 (15.0 g, 27.1 mmol) and2-chloro-4,6-diphenyl-1,3,5-triazine (7.2 g, 27.1 mmol) intotetrahydrofuran (150 ml), a 2 M aqueous potassium carbonate solution(aq. K₂CO₃) (40 ml) and then tetrakis(triphenyl-phosphine)palladium(0)[Pd(PPh₃)₄] (0.9 g, 3 mol %) were added thereto, and the result wasstirred under reflux for 4 hours. The temperature was lowered to roomtemperature, and produced solids were filtered. The filtered solids wererecrystallized with tetrahydrofuran and ethyl acetate, filtered, andthen dried to prepare Compound 4 (6.7 g, yield 36%; MS: [M+H]⁺=670).

Preparation Example 5

1) Synthesis of Compound 5-1

Compound 1-3 (20.0 g, 60.8 mmol) and 9H-carbazole (10.2 g, 60.8 mmol)were introduced to xylene (200 mL) for dissolution, and sodiumtertiary-butoxide (17.5 g, 182.4 mmol) was added thereto, and thetemperature was raised. Bis(tri-tertiary-butylphosphine)palladium (1.0g, 3 mol %) was introduced thereto, and the result was stirred underreflux for 12 hours. When the reaction was completed, the temperaturewas lowered to room temperature, and produced solids were filtered. Thesolids were dissolved in chloroform (700 mL), and after washed twicewith water, the organic layer was separated, stirred after introducinganhydrous magnesium sulfate thereto, and filtered, and the filtrate wasvacuum distilled. The concentrated compound was purified through silicacolumn using chloroform and ethyl acetate to prepare Compound 5-1 (19.4g, 69%; MS: [M+H]⁺=463) in a light green solid form.

2) Synthesis of Compound 5-2

Compound 5-1 (19.4 g, 39.0 mmol) bis(pinacolato)diboron (11.7 g, 46.0mmol), potassium acetate (11.5 g, 116.8 mmol), dibenzylideneacetonepalladium (0.7 g, 1.2 mmol) and tricyclohexylphosphine (0.7 g, 2.4 mmol)were introduced to dioxane (200 ml), and refluxed for 12 hours. Afterthe reaction was finished, the result was cooled to room temperature andthen vacuum distilled to remove the solvent. This was dissolved inchloroform, washed 3 times with water, and the organic layer wasseparated and dried with magnesium sulfate. This was recrystallizedusing ethyl acetate while being vacuum distilled to prepare Compound 5-2(17.5 g, yield 81%; MS: [M+H]⁺=555).

3) Synthesis of Compound 5

After dispersing Compound 5-2 (15.0 g, 27.1 mmol) and2-chloro-4,6-diphenyl-1,3,5-triazine (7.2 g, 27.1 mmol) intotetrahydrofuran (150 ml), a 2 M aqueous potassium carbonate solution(aq. K₂CO₃) (40 ml) and then tetrakis(triphenyl-phosphine)palladium(0)[Pd(PPh₃)₄] (0.9 g, 3 mol %) were added thereto, and the result wasstirred under reflux for 4 hours. The temperature was lowered to roomtemperature, and produced solids were filtered. The filtered solids wererecrystallized with tetrahydrofuran and ethyl acetate, filtered, andthen dried to prepare Compound 5 (6.7 g, yield 36%; MS: [M+H]⁺=670).

Experimental Example Example 1

A glass substrate on which indium tin oxide (ITO) was coated as a thinfilm to a thickness of 1,300 Å was placed in distilled water containingdissolved detergent and ultrasonically cleaned. A product of Fischer Co.was used as the detergent, and as the distilled water, distilled waterfiltered twice with a filter manufactured by Millipore Co. was used.After the ITO was cleaned for 30 minutes, ultrasonic cleaning wasrepeated twice using distilled water for 10 minutes. After the cleaningwith distilled water was finished, the substrate was ultrasonicallycleaned with solvents of isopropyl alcohol, acetone and methanol, thendried, and then transferred to a plasma cleaner. The substrate wascleaned for 5 minutes using oxygen plasma, and then transferred to avacuum deposition apparatus.

On the transparent ITO electrode prepared as above, a hole injectionlayer was formed by thermal vacuum depositing the following HI-1compound to a thickness of 50 Å. On the hole injection layer, a holetransfer layer was formed by thermal vacuum depositing the followingHT-1 compound to a thickness of 250 Å, and on the HT-1 deposited film,an electron blocking layer was formed by vacuum depositing the followingHT-2 compound to a thickness of 50 Å. On the HT-2 deposited film,Compound 1 prepared in advance in Preparation Example 1, the followingYGH-1 compound and phosphorescent dopant YGD-1 were co-deposited in aweight ratio of 44:44:12 to form a light emitting layer having athickness of 400 Å. An electron transfer layer was formed on the lightemitting layer by vacuum depositing the following ET-1 compound to athickness of 250 Å, and on the electron transfer layer, an electroninjection layer having a thickness of 100 Å was formed by vacuumdepositing the following ET-2 compound and Li in a weight ratio of 98:2.A cathode was formed on the electron injection layer by depositingaluminum to a thickness of 1000 Å.

In the above-mentioned process, the deposition rates of the organicmaterials were maintained at 0.4 Å/sec to 0.7 Å/sec, the deposition rateof the aluminum was maintained at 2 Å/sec, and the degree of vacuumduring the deposition was maintained at 1×10-? torr to 5×10⁻⁸ torr.

Experimental Examples 2 to 5

Organic light emitting devices were manufactured in the same manner asin Experimental Example 1 except that compounds described in thefollowing Table 1 were used instead of Compound 1 of Preparation Example1.

Comparative Experimental Examples 1 to 3

Organic light emitting devices were manufactured in the same manner asin Experimental Example 1 except that compounds described in thefollowing Table 1 were used instead of Compound 1 of PreparationExample 1. Compounds of CE1 to CE3 of the following Table 1 are asfollows:

For the organic light emitting devices manufactured in the experimentalexamples and the comparative experimental examples, voltage andefficiency were measured at a current density of 10 mA/cm², and alifetime was measured at a current density of 50 mA/cm². The results areshown in the following Table 1. Herein, LT95 means time taken forluminance becoming 95% with respect to initial luminance.

TABLE 1 Voltage Efficiency Color Lifetime (h) (V) (@10 (Cd/A) (@10Coordinate (LT₉₅ at 50 Compound mA/cm²) mA/cm²) (x, y) mA/cm²)Experimental Compound 1 4.2 84 0.45, 0.54 110 Example 1 ExperimentalCompound 2 3.8 83 0.46, 0.53 115 Example 2 Experimental Compound 3 4.179 0.45, 0.53 170 Example 3 Experimental Compound 4 3.9 82 0.45, 0.54155 Example 4 Experimental Compound 5 3.8 82 0.45, 0.54 180 Example 5Comparative CE1 4.5 70 0.46, 0.54 90 Experimental Example 1 ComparativeCE2 6.0 34 0.48, 0.50 5 Experimental Example 2 Comparative CE3 5.5 740.45, 0.57 40 Experimental Example 3

As shown in Table 1, it was identified that, when using the compound ofthe present disclosure as a light emitting layer material, properties ofexcellent efficiency and lifetime were obtained compared to thecomparative experimental examples. This is due to excellent materialstability obtained by bonding benzothiopyrimidine to a triazine unit,which leads to excellent device efficiency, lifetime or the like. Inaddition, it was seen that those additionally substituted withacarbazole group had excellent lifetime properties, and thosesubstituted with only an aryl substituent had excellent efficiency.

1. A compound of Chemical Formula 1:

wherein, in Chemical Formula 1: Y is O or S; X1 to X3 are each N or CH,and one or more of X1 to X3 is N; and Ar1 to Ar4 are the same as ordifferent from each other, and each independently is an aryl grouphaving 6 to 20 carbon atoms that is unsubstituted or substituted withnitrile or a heteroaryl group having 2 to 20 carbon atoms; or atricyclic heteroaryl group having 2 to 20 carbon atoms that isunsubstituted or substituted with an aryl group having 6 to 20 carbonatoms.
 2. The compound of claim 1, wherein X1, X2 and X3 are N.
 3. Thecompound of claim 1, wherein X1 is CH, and X2 and X3 are N; or X2 is CH,and X1 and X3 are N.
 4. The compound of claim 1, wherein Ar1 to Ar4 arethe same as or different from each other, and each independently is aphenyl group that is unsubstituted or substituted with a nitrile groupor a carbazole group; a biphenylyl group; a carbazole group that isunsubstituted or substituted with a phenyl group; a dibenzofuran group;or a dibenzothiophene group.
 5. The compound of claim 1, wherein thecompound of Chemical Formula 1 is selected from among the followingcompounds:


6. An organic light emitting device comprising: a first electrode; asecond electrode provided opposite to the first electrode; and one, twoor more organic material layers provided between the first electrode andthe second electrode, wherein one or more layers of the organic materiallayers include the compound of claim
 1. 7. The organic light emittingdevice of claim 6, wherein the organic material layer includes a lightemitting layer, and the light emitting layer includes the compound.